Spectroscopic,morphological, and mechanistic investigation of the solvent- promoted aggregation of porphyrins modified in meso-positions by glucosylated steroids (Articolo in rivista)

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  • Spectroscopic,morphological, and mechanistic investigation of the solvent- promoted aggregation of porphyrins modified in meso-positions by glucosylated steroids (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.201101163 (literal)
Alternative label
  • K. Zelenka, T. Trnka, I. Tislerova, D. Monti, S. Cinti, M.L. Naitana, L. Schiaffino, M. Venanzi, G. Laguzzi, L. Luvidi, G. Mancini, Z. Novakova, O. Simak, Z. Wimmer, P. Drasar (2011)
    Spectroscopic,morphological, and mechanistic investigation of the solvent- promoted aggregation of porphyrins modified in meso-positions by glucosylated steroids
    in Chemistry - A European Journal; WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim (Germania)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • K. Zelenka, T. Trnka, I. Tislerova, D. Monti, S. Cinti, M.L. Naitana, L. Schiaffino, M. Venanzi, G. Laguzzi, L. Luvidi, G. Mancini, Z. Novakova, O. Simak, Z. Wimmer, P. Drasar (literal)
Pagina inizio
  • 13743 (literal)
Pagina fine
  • 13753 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.wiley (literal)
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  • 17 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#note
  • ISSN: 0947-6539 (literal)
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  • 11 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Charles University, Department of Organic Chemistry Albertov 8, 12840 Prague 2 (Czech Republic) Department of Natural Compounds Chemistry Institute of Chemical Technology Prague Technick? 5, 16628 Prague 6 (Czech Republic) University of Rome Tor Vergata Department of Chemical Technologies Via della Ricerca Scientifica 1, 00133, Rome (Italy) IMR-CNR, c/o Department of Chemistry, University of Rome La Sapienza, P.le A. Moro 5, 00185, Rome (Italy) Institute of Experimental Botany AS CR vvi, Isotope Laboratory Vden? sk 1083, 142 20 Prague 4 (Czech Republic) (literal)
Titolo
  • Spectroscopic,morphological, and mechanistic investigation of the solvent- promoted aggregation of porphyrins modified in meso-positions by glucosylated steroids (literal)
Abstract
  • Solvent-driven aggregation of a series of porphyrin derivatives was studied by UV/Vis and circular dichroism spectroscopy. The porphyrins are characterised by the presence in the meso positions of steroidal moieties further conjugated with glucosyl groups. The presence of these groups makes the investigated macrocycles amphiphilic and soluble in aqueous solvent, namely, dimethyl acetamide/ water. Aggregation of the macrocycles is triggered by a change in bulk solvent composition leading to formation of large architectures that express supramolecular chirality, steered by the presence of the stereogenic centres on the periphery of the macrocycles. The aggregation behaviour and chiroptical features of the aggregates are strongly dependent on the number of moieties decorating the periphery of the porphyrin framework. In particular, experimental evidence indicates that the structure of the steroid linker dictates the overall chirality of the supramolecular architectures. Moreover, the porphyrin concentration strongly affects the aggregation mechanism and the CD intensities of the spectra. Notably, AFM investigations reveal strong differences in aggregate morphology that are dependent on the nature of the appended functional groups, and closely in line with the changes in aggregation mechanism. The suprastructures formed at lower concentration show a network of long fibrous structures spanning over tens of micrometres, whereas the aggregates formed at higher concentration have smaller rodshaped structures that can be recognised as the result of coalescence of smaller globular structures. The fully steroid substituted derivative forms globular structures over the whole concentration range explored. Finally, a rationale for the aggregation phenomena was given by semiempirical calculations at the PM6 level. (literal)
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